Reilly studied Womenswear and Cultural Studies at the London College of Fashion, and later pursued Accessory Design at the Fashion Institute of Technology in New York. After leaving formal institutions, she apprenticed with a master cordwainer in Hungary and conducted extensive research in France, Southern Italy, and Ireland. She now lives and works at Benedictine Farm, where her studio is surrounded by the agricultural rhythms that inform her practice. When not tending her gardens, she continues a seven-year apprenticeship with a master cordwainer in Pennsylvania. She is a 2022–2025 recipient of the Folk and Traditional Arts Grant from the Pennsylvania Council on the Arts.